Orange azo dye.



- UNITED sra'rns rATE T OFFICE.

KARL scHNr'rzsPAHN, or oFFENBacn-oN- rriE-MAIN, GER ANY. AssIGNois j'ro con PORATION or cmaivrlsone FABRI'K GRIESI-IEIM-ELEK'IRON, or ERANKFORT-ON- THE-MAIN, GERMANY.

No Drawing To all whom 'it may concern:

vleit known that I, Kant, Sonxrrzsmnx, doctor of philosophy, chemist, a subject of the German Emperor, and resident, of Offenbach-on-tlie-Main, in the Grand Duchyot' Hessen, 'Gcrniany, with the post'-ottice address ()bcrmainstrasso No. 81, have ii rented new and useful Improvements in Orange .izmDVes. of which thefollowing is-especi fication.

The invention relates to the manufacture of new azo coloring' nia-tter by combining the diazo compounds ot'.amins ot' the general formula:

C I I XA ZNI-I wherein X, Y and Z means H, Cl and 80,11 and wherein at least one of these substituents is a chlorin atom, with beta-naphthylamin-sul't'onic acids having the formula:

, O, H .X.NH,.SO,H ("X-meaning H or H30 It is also found that-these dyestuffs are very suitable for the manufacture of pigment' colors.

. These dyestuffs dye very bright orange shades. The dyestuffs obtained trom amins containing two or three chlorin atoms, or one or two chlorin atoms and one sulfonic group, show a remarkable -itastness against the action of acids and lightl The following examples will serve to' illustrate the nature of the invention. The parts are by weight.

Example 1: 128 parts ofpara-chloroani- 1111 are dissolved in 640 parts of water and 34:2 parts of hydrochloric acid (20 B.)

and diazotized with 280 parts of a solution containing 25 per cent. of sodium nitrite.

The diazo solution is combined at a temperature of C. with a solution of 360 parts of theneutral sodium saltof 22:316-- naphthylamindisulfon-ic acid containing 272 parts of crystallized sodium acetate. After the formation of the dyestuff the mixture isanilin are suflieiently ground with 400 parts:

ORANGE .AZO )QYE.

Specification of Letters Patent. HILaZl-efifd May 2-1, Application filed -August 4,:1 S,O 9 L Serial No; 511.107. i v

' offhydrochloric acid ll.) and after additionof-alOO parts of ice diazotized with 280' parts of a solution containingpet" cent. otsodium nitrite. ".lhe dia-zo solution is allowed. to flow into a solution of 360 parts of the neutral sodium salt of 2:3:(3- naphthylair-indisnltonic acid. .Htcr the formation of the dyestutt 170 parts of calcined. I sodium carbonate are'added. Themixture is heated up to boiling'and the dyestullprecipitated by meansof common salt. The' thus obtained coloring matter forms in dry shape an orange-yellow powder, soluble in concentrated sulfuric acid with blue-red color, in water with orange-yellow color, which is not changed by addition of hydrochloric acid or caustic soda lye. Example 3: 264 parts of the sodium salt. I of 2:5-dichloroanilin-ehsulfonic' acid are diazotized in the usual manner with 1200 parts of water, 342 parts of hydrochloric.

acid (20.B.) and 280partsot a solution containing 25 per cent. of -sodinmnitrite-- The .diazo solution is added to a solution containing 360 parts'of the neutral sodium salt of 2:3:6-naphthylamindisultonicacid and 136 parts of crystallized sodium acetate.

lVhen the formation of the dyestnfi iscompletpflt-he coloring matter is precipitated by I addition ofconnnon salt. -The dyestufi' thus 35 resulting forms an orange yellow soluble in concentrated sulfuric'ac red color, in water with ora ngesyellowf -c 'olor, which is i'iot changedbyaddition of hydrochloric acid or ca'usticsoda lye. 7 o; Exa1nple 4cr162 parts of 2: 5 dichloro'arn lin are diazotized according to the st:'a-t meuts given in Example 2. The diazo sol-u tion is added to a solution cQnt'ainii'ig-BSO parts of the neutral sodium salt of 2 25:! naphthylaniindisulfonic acid and 272 parts of crystallized sodium acetate. After formation of the dyestufi the mixture is heated up and the dyestnlf precipitated by means 0 common salt. The coloring mattcr re 1 00 suiting forms in dry state an orange yellow powder, soluble in concentrated sulfuric acid with blue-red color, in water with orange-yellow color, which is not changed by addition of hydrochloric:acid or caustic soda'lye. v

Instead of the amins, used in the above-- mentioned processes, ortho-chloroanilin, 3 :4 dichloroanilin, 2:415 :1 trichloroanilin,

monochloroanilinsulfonic acid and 3:4-diter obtained be used.

chloroanilin sulfonic acid, respectively instead of 2:3 :6-naphthylamindisulfonic acid, 2 :5 :7-naphthylaniindisulfonic acid and 2:6- or 2 :5-naphthylan1inmonosulfonic acid may Now what I claim and. desire tosecure by Letters Patent is.the following:

1. The I process for the 'manufactur of new 'monoazodyestuifs, which consists in combining the diazo compounds of-ami-ns of the general formula:

wherein Y and Z means H, Cl and S0511, and wherein-at least one of these subst-iti ents is a ,chlorin atom, with beta-naphthylammsulfonic acids of the formula:

o H .X.N .s'o,H- wherein X means Hand 'SO H. I

2. As new pounds of amins of the general formula o 'H .X.Y.z.NH,' wherein Y and Z means H, Cl and SO H, and whereintatleast-one of these sub stituents is a chlorin atom, with beta-naphthylaniinsulfonic acrdsof the formula:

, o ngxnrr so n wherein X means-H and SO H, which in the shape of its alkaline salt is an orange yellow powder, soluble in water with orange-- yellow color, in concentrated sulfuric acid with yellowish to bluish Bordeaux red color.-

products, the. azo coloring maty combining the diazocon'r.

coloring"mattn'pbt'ained by combining the diazo coinpounidjsflof amins having the gen-- eral formula:

wherein X, Y and Z means H, Cl and S0 11, and wherein at least one of these substituents is achlorin' atom, with 2-naphthyl'amin-3 :6- disulfonic acid, -which coloring matter is 'in the shape of itsalkaline salt an orange yel-' lowpowder, soluble in concentratedsulfuric acid with Bordeaux-red to violet color, in water with orange-yellow color, which is-not changed by addition of hydrochloric acid or caustic soda lye.

5. The processfor'themanufactureofnew inoiioazodyestufi's which consists in combin mg dlchloroanlhn w1th disulfo'nic acid.

'6. As new p'roducts the'dyestuifs obtained 2-naphthylamin-3 :6- v I by combining dichloroanilinwith 2-naphthylv amin-3 :6-disulfonic'acid, which'are in shape of their alkaline salts orange-yellow powders solublein concentrated sulfuric acid'lwith 'bluerred color, in'water with orange-yellow color, which is not changed by addition-of hydrochloric acid "or caustic soda lye.-

7.: The process of manufacturing new mono-azo coloring matter, which consists 1n combinmg 2 :5-d1chloro-an1lm WIth 2-naphthylam'in-3 :G-disulfonic' acid.

8. As'a new product the dyestuff obtained by combining 2:5-dichlor'o-anilin With- 2- na-phthylamin-3zfi-disulfonic acid, which dyestuff is in the shape of its alkaline salt an orange-yellow powder, soluble in concentra-ted sulfuric acid with blue-red color, in

water with orange-yellow color, which is not changed by addition of hydrochloric acld or caustic soda'lye.

In testimony, that I claimthe foregoing as my intention, I have signed my name inresence of two witnesses, th s 26th day of July 1909.

' KARL soHNITZsPAHN.

Witnesses:

JEAN GRUND, A CARL GRUND. 

